WO2016064110A1 - Dispositif électronique organique et appareil d'affichage utilisant une composition pour dispositif électronique organique - Google Patents

Dispositif électronique organique et appareil d'affichage utilisant une composition pour dispositif électronique organique Download PDF

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WO2016064110A1
WO2016064110A1 PCT/KR2015/010541 KR2015010541W WO2016064110A1 WO 2016064110 A1 WO2016064110 A1 WO 2016064110A1 KR 2015010541 W KR2015010541 W KR 2015010541W WO 2016064110 A1 WO2016064110 A1 WO 2016064110A1
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compound
organic
compounds
electronic device
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Korean (ko)
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이문재
박정철
문성윤
권재택
이범성
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덕산네오룩스 주식회사
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Priority to CN201580057682.2A priority Critical patent/CN107004770B/zh
Priority to US15/521,463 priority patent/US20170317289A1/en
Publication of WO2016064110A1 publication Critical patent/WO2016064110A1/fr

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Definitions

  • the present invention relates to an organic electronic device, a display device, and an electronic device using a composition made of a compound for an organic electric device, and more particularly, to a display device including an organic material layer in which two or more different hole transport materials are used in the hole transport layer. And an organic electric element.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using organic materials.
  • An organic electroluminescent device using an organic light emitting phenomenon is a self-light emitting device using a principle that a light emitting material emits light by recombination energy of holes injected from an anode and electrons injected from a cathode by applying a current.
  • the organic electroluminescent device has an anode formed on the substrate, and may have a structure in which a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode are sequentially formed on the anode.
  • the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron injection layer is an organic thin film made of an organic compound.
  • the driving voltage problem and the lifetime problem are very related to the thermal deterioration problem of the hole injection material and the hole transport material.
  • a method of constructing a hole transport layer in multiple layers US Pat. No. 5,569,45
  • a method of using a material having a high glass transition temperature US Pat. No. 5,506,569 have been proposed.
  • the present invention mixes two or more hole transport materials having different band gaps in the hole transport layer to increase the lifespan by reducing thermal degradation occurring at the interface between the hole injection layer and the hole transport layer and the interface between the hole transport layer and the light emitting layer,
  • An object of the present invention is to provide an organic electric device having an excellent luminous efficiency by efficiently adjusting the injection amount of charge resistance.
  • the present invention is a first electrode; Second electrode; And an organic material layer disposed between the first electrode and the second electrode, the organic material layer including a light emitting layer including a hole transport layer and a light emitting compound, wherein the hole transport layers are mutually structured among the compounds represented by Formula 1 below.
  • a display device comprising a composition in which two different compounds are mixed.
  • the present invention also relates to an organic electronic device using the composition in which the compound for an organic electronic device represented by Formula 1 is mixed, and an electronic device thereof. More specifically, two or more different hole transport materials are mixed in the hole transport layer. An organic electronic device using the composition and an electronic device including the same are provided.
  • thermal degradation occurring at the interface between the hole injection layer and the hole transport layer and the interface between the hole transport layer and the light emitting layer is reduced, and thus the lifetime is long. This efficiency is adjusted to provide excellent luminous efficiency.
  • FIG. 1 is an exemplary view of an organic electric device according to an embodiment of the present invention.
  • halo or halogen as used herein is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise indicated.
  • alkyl or “alkyl group” has a single bond of 1 to 60 carbon atoms, unless otherwise indicated, and is a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted cyclo Radicals of saturated aliphatic functional groups, including alkyl groups, cycloalkyl-substituted alkyl groups.
  • alkenyl group As used herein, the terms “alkenyl group”, “alkenyl group” or “alkynyl group” have a double or triple bond of 2 to 60 carbon atoms, respectively, unless otherwise stated, and include straight or branched chain groups. It is not limited to this.
  • alkoxyl group means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, and is limited herein. It is not.
  • aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
  • an aryl group or an arylene group means an aromatic of a single ring or multiple rings, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction.
  • the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.
  • aryl or "ar” means a radical substituted with an aryl group.
  • an arylalkyl group is an alkyl group substituted with an aryl group
  • an arylalkenyl group is an alkenyl group substituted with an aryl group
  • the radical substituted with an aryl group has the carbon number described herein.
  • an arylalkoxy group means an alkoxy group substituted with an aryl group
  • an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group
  • an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group.
  • the arylcarbonyl group is a carbonyl group substituted with an aryl group.
  • heterocyclic group includes one or more heteroatoms, unless otherwise indicated, and has from 2 to 60 carbon atoms, and includes at least one of single and multiple rings, heteroaliphatic rings and hetero Aromatic rings. Adjacent functional groups may be formed in combination.
  • heteroatom refers to N, O, S, P or Si unless otherwise stated.
  • a “heterocyclic group” may also include a ring containing SO 2 in place of the carbon forming the ring.
  • a “heterocyclic group” includes the following compounds.
  • aliphatic as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms
  • aliphatic ring means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
  • ring refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms or an aromatic ring having 6 to 60 carbon atoms or a hetero ring having 2 to 60 carbon atoms or a combination thereof. Saturated or unsaturated rings.
  • heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
  • substituted in the term “substituted or unsubstituted” as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 1 ⁇ C 20 alkoxyl group, C 1 ⁇ C 20 alkylamine group, C 1 ⁇ C 20 alkylthiophene group, C 6 ⁇ C 20 arylthiophene group, C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 20 alkynyl, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 20 aryl group, of a C 6 ⁇ C 20 substituted by deuterium aryl group, a C 8 ⁇ C 20 aryl alkenyl group, a silane group, a boron Group, germanium group, and C 2 ⁇ C 20 It is meant to be substituted with one or more substituents selected from the group consist
  • the substituent R 1 when a is an integer of 0, the substituent R 1 is absent, when a is an integer of 1, one substituent R 1 is bonded to any one of carbons forming the benzene ring, and a is an integer of 2 or 3 are each bonded as follows, where R 1 may be the same or different from each other, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bonded to the carbon forming the benzene ring Is omitted.
  • the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.
  • OLED organic electroluminescent device
  • OPC organic photoconductor
  • organic TFT organic transistor
  • Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
  • the present invention is a first electrode; Second electrode; And an organic material layer disposed between the first electrode and the second electrode, the organic material layer including a light emitting layer including a hole transport layer and a light emitting compound, wherein the hole transport layer comprises two kinds of arylamine compounds having different structures from each other.
  • a display device comprising the mixed composition, wherein the compound ratio of each different structural formula is selected from 5: 5 to 9: 1.
  • the hole transport layer provides a display device comprising a composition in which two compounds having different structures from each other are represented by Formula 1 below.
  • Ar 1 ⁇ Ar 3 is selected from the group consisting of a heteroaryl group, fluorene-carbonyl of C 6 ⁇ 60 aryl group, C 2 ⁇ 60 of the, L 1 ⁇ L 3 represents a single bond, C 6 ⁇ It is selected from the group consisting of a 60 arylene group, a divalent C 2 to 60 heterocyclic group, a fluorenylene group, a C 3 to 60 aliphatic ring and a C 6 to 60 aromatic ring divalent fused ring group.
  • aryl group, heteroaryl group, fluorenyl group, arylene group, heterocyclic group and fused ring group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; -LN (R a) (R b) ; C 1 ⁇ Import alkylthio of C 20; C 1 ⁇ alkoxy group of C 20; C 1 ⁇ alkyl group of C 20; C 2 ⁇ of the C 20 alkenyl; C 2 ⁇ C 20 the alkynyl group; an aryl group of a C 6 ⁇ C 20 substituted with heavy hydrogen;; C 6 ⁇ C 20 aryl group, a fluorenyl group; C 2 ⁇ heterocyclic group of C 20; C 3 ⁇ cycloalkyl group of C 20; C May be further substituted with one or more substituents selected from the group consisting of 7 to C 20 arylalkyl groups and
  • the first electrode Second electrode; And an organic material layer disposed between the first electrode and the second electrode, the organic material layer including at least one hole transport layer and a light emitting layer, wherein the hole transport layer is different from each other in the structure represented by Chemical Formula 1.
  • an organic electric device comprising a composition in which two compounds are mixed.
  • At least one of the two compounds represented by the formula (1) provides an organic electric device, characterized in that represented by the following formulas 1-2, 1-3, 1-4.
  • X, Y, Z is S, O
  • CR ', R ", R ', R” is selected from the group consisting of C 6-24 aryl group, C 1-20 alkyl group, C 2-20 alkenyl, C 1 -C 20 alkoxy group, R', R " May combine to form a spy
  • R 1 ⁇ R 6 is selected from the group consisting of deuterium, tritium, cyano group, nitro group, halogen group, aryl group, alkenyl group, alkylene group, alkoxy group, heterocyclic group
  • R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 combine with each other to form a ring
  • l, n, and p represent an integer of 0-3, m, o, q is an integer from 0-4.
  • Another specific example of the present invention provides an organic electric device including the composition represented by Chemical Formula 1 as the following compound.
  • an organic electric device consisting of a composition containing a compound in which Ar 1 , Ar 2 , Ar 3 of the two compounds represented by Formula 1 are all C 6-24 aryl groups.
  • Ar 1 , Ar 2 , Ar 3 of one compound of the two compounds represented by Formula 1 above are all C 6-24 aryl groups;
  • At least one of Ar 1 , Ar 2 , Ar 3 of each of the two compounds represented by Formula 1 includes a composition comprising a compound consisting of dibenzothiophene or dibenzofuran, and a display including the same Providing a device.
  • an organic electric device comprising a composition having a ratio of 10% to 90% when a compound of any one of two compounds having different structures represented by Chemical Formula 1 is mixed with each other, and comprising the same A display device is provided.
  • the mixing ratio is 5: 5 or 6: 4 or 7: 3 or 8: 2 or 9
  • an organic electric device comprising a composition further comprising at least one compound represented by Formula 1 in a mixture in which compounds having different structures represented by Formula 1 are mixed with each other;
  • a display device including the same is provided.
  • an organic electric device characterized in that the compound represented by the formula (1) as a light emitting auxiliary layer between the hole transport layer and the light emitting layer used by mixing two different compounds represented by the formula (1) different from each other. It provides an organic electric device further comprising a light efficiency improvement layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.
  • the organic layer may be formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, or a roll-to-roll process.
  • the present invention provides an electronic device including a display device including the organic electronic device of various examples described above and a control unit for driving the display device.
  • the organic electroluminescent device may be applied to an electronic device characterized in that the organic electroluminescent device, an organic solar cell, an organic photoconductor, an organic transistor, and a device for monochrome or white illumination.
  • Sub 2 of Scheme 1 may be synthesized by the reaction path of Scheme 2 or Scheme 3 below, but is not limited thereto.
  • naphthalen-1-amine (15 g, 104.8 mmol), 2-bromodibenzo [b, d] thiophene (30.3 g, 115.2 mmol), Pd 2 (dba) 3 (4.8 g, 5.24 mmol), P ( t-Bu) 3 (2.12 g, 10.48 mmol), NaOt-Bu (460.9 g, 345.7 mmol) and toluene (1100 mL) were tested in the same manner as in Sub 2-1 to obtain 24.9 g of Sub 2-40.
  • Sub 2-1 to Sub 2-52 were synthesized by the same method as the synthesis method, and Sub 2 is not limited thereto.
  • di ([1,1'-biphenyl] -4-yl) amine (10 g, 31.1 mmol), 4-bromo-1,1'-biphenyl (8 g, 34.2 mmol), Pd 2 (dba ) 3 (1.42 g, 1.56 mmol), P (t-Bu) 3 (0.63 g, 3.11 mmol), NaOt-Bu (136.9 g, 102.7 mmol) and toluene (330 mL) were added followed by reaction at 100 ° C. do.
  • N-([1,1'-biphenyl] -4-yl) -9,9'-spirobi [fluoren] -2-amine (10 g, 20.7 mmol), 2-bromodibenzo [b, d] thiophene (6 g, 22.7 mmol), Pd 2 (dba) 3 (0.95 g, 1.03 mmol), P (t-Bu) 3 (0.42 g, 2.07 mmol), NaOt-Bu (91 g, 68.2 mmol), toluene (220 mL) was experimented in the same manner as in 1-1 ', to obtain 10.2 g of Product 1-24'. (Yield 74%)
  • N-([1,1'-biphenyl] -4-yl) benzo [4,5] thieno [3,2-d] pyrimidin-2-amine (10 g, 28.3 mmol), 4- ( 4-bromophenyl) dibenzo [b, d] furan (10.1 g, 31.1 mmol), Pd 2 (dba) 3 (1.3 g, 1.41 mmol), P (t-Bu) 3 (0.57 g, 2.83 mmol), NaOt- Bu (124.5 g, 93.4 mmol) and toluene (300 mL) were tested in the same manner as in 1-1 'to obtain 12.3 g of Product 1-59'. (Yield: 73%)
  • the synthesis method is based on the Buchwald-Hartwing cross coupling reaction.
  • Example I-1 Blue Organic Electroluminescent device ( Hole transport layer )
  • An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a hole transport layer material.
  • 2-TNATA 4,4 ', 4''-Tris [2-naphthyl (phenyl) amino] triphenylamine
  • a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by doping 9,10-di (naphthalen-2-yl) anthracene, or BD-052X (Idemitsukosan) as a dopant at 95: 5 weight on the hole transport layer.
  • BD-052X Imdemitsukosan
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum
  • a hole blocking layer was formed, and tris (8-quinolinol) aluminum (hereinafter abbreviated as "Alq 3 ”) was vacuum deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm to form an electron injection layer, and then an Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
  • Alq 3 tris (8-quinolinol) aluminum
  • An organic electroluminescent device was manufactured in the same manner as in Example I-1, except that Comparative Compounds 1 to 4 were used instead of the mixture of the present invention as the hole transport layer material.
  • the electroluminescence (EL) characteristics of the organic electroluminescent devices prepared according to Examples and Comparative Examples 1 to 4 were prepared by applying a forward bias DC voltage to the photoresearch company PR-650.
  • the T95 lifetime was measured using a life-time measuring instrument manufactured by McScience Inc. at a luminance of 500 cd / m 2.
  • the following table shows the results of device fabrication and evaluation.
  • tertiary amines all substituted with aryl groups biphenyl are tertiary amines having different structures from tertiary amines (comparative compounds 1-3 ', 1-4', 1). -9 ', 1-10', 1-12 ', 1-14', 1-17 ', 1-19', 1-25 ', 1-26', 1-48 ', 1-52', 1 -57 ', 1-72')
  • tertiary amines (1-3 ', 1-4', 1-9 ', 1- which are substituted with simple aryls and have different structures than those of Comparative Compound 2, in which all of the amine substituents are aryl groups, are used as a single compound).

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Abstract

La présente invention concerne un dispositif électronique organique et un appareil d'affichage, ainsi qu'un appareil électronique équipé de ceux-ci, le dispositif électronique organique comportant une couche de transport de trous qui comprend une composition constituée d'au moins deux composés présentant des structures similaires, et ledit dispositif étant ainsi caractérisé par une meilleure efficacité d'émission de lumière, une plus grande stabilité et une durée de vie prolongée.
PCT/KR2015/010541 2014-10-24 2015-10-06 Dispositif électronique organique et appareil d'affichage utilisant une composition pour dispositif électronique organique WO2016064110A1 (fr)

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018048128A (ja) * 2016-09-14 2018-03-29 株式会社半導体エネルギー研究所 有機化合物、発光素子、発光装置、電子機器、及び照明装置
CN107915648A (zh) * 2016-10-11 2018-04-17 东进世美肯株式会社 新颖化合物及包含其的有机发光器件
CN108250083A (zh) * 2016-12-27 2018-07-06 东进世美肯株式会社 新颖化合物及包含其的有机发光器件
CN108383734A (zh) * 2017-02-03 2018-08-10 三星显示有限公司 胺类化合物和包括该胺类化合物的有机发光器件
US11121329B2 (en) 2017-11-24 2021-09-14 Samsung Display Co., Ltd. Amine compound and organic electroluminescence device including the same
US11380846B2 (en) * 2015-05-27 2022-07-05 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element comprising the same and electronic device thereof
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Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106660966B (zh) * 2014-05-22 2020-04-10 德山新勒克斯有限公司 有机电气元件用化合物、利用其的有机电气元件及其电子装置
KR102545858B1 (ko) * 2014-07-11 2023-06-21 이데미쓰 고산 가부시키가이샤 화합물, 유기 전기발광 소자용 재료, 유기 전기발광 소자, 및 전자 기기
JP6506534B2 (ja) 2014-11-07 2019-04-24 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機電界発光素子用材料及びこれを用いた有機電界発光素子
JP6600495B2 (ja) 2015-06-17 2019-10-30 三星ディスプレイ株式會社 有機電界発光素子用材料及びこれを用いた有機電界発光素子
US20200290986A1 (en) * 2015-06-17 2020-09-17 Samsung Display Co., Ltd. Mono amine derivatives and organic electroluminescent device including the same
KR102560940B1 (ko) * 2015-06-17 2023-08-01 삼성디스플레이 주식회사 모노 아민 유도체 및 이를 포함하는 유기 전계 발광 소자
JP6661289B2 (ja) * 2015-07-08 2020-03-11 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
WO2017022730A1 (fr) * 2015-07-31 2017-02-09 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique, et dispositif électronique
US10439146B2 (en) * 2015-08-07 2019-10-08 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting element, light-emitting device, electronic device, and lighting device
CN108369996B (zh) * 2015-12-17 2021-07-09 株式会社半导体能源研究所 发光元件、发光装置、电子设备、照明装置、照明系统及引导系统
KR102635702B1 (ko) * 2016-01-11 2024-02-15 덕산네오룩스 주식회사 유기발광소자, 유기발광 표시장치 및 유기발광소자용 화합물
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KR20220007306A (ko) * 2020-07-10 2022-01-18 주식회사 동진쎄미켐 신규 화합물 및 이를 포함하는 유기 발광 소자
CN117177600A (zh) * 2020-12-28 2023-12-05 京东方科技集团股份有限公司 显示装置
US20230078029A1 (en) * 2021-01-28 2023-03-16 Samsung Display Co., Ltd. Luminescence device and amine compound for luminescence device
CN112961131A (zh) * 2021-02-04 2021-06-15 吉林奥来德光电材料股份有限公司 有机化合物、其制备方法和应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5804322A (en) * 1995-11-17 1998-09-08 Motorola, Inc. Organic electroluminescence device with mixed hole transporting materials
KR20110029831A (ko) * 2009-09-16 2011-03-23 주식회사 진웅산업 유기 발광 화합물 및 이를 이용한 유기 전계발광 소자
KR20130121516A (ko) * 2012-04-27 2013-11-06 (주)위델소재 신규한 아릴아민을 사용한 정공 수송 물질 및 이를 포함한 유기 전계 발광 소자

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080238300A1 (en) * 2007-04-02 2008-10-02 Sang Tae Park Organic electroluminescence device and method for fabricating the same
JP5515661B2 (ja) * 2009-11-16 2014-06-11 ソニー株式会社 有機ｅｌ表示装置の製造方法
KR101311935B1 (ko) * 2010-04-23 2013-09-26 제일모직주식회사 유기광전소자용 화합물 및 이를 포함하는 유기광전소자

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5804322A (en) * 1995-11-17 1998-09-08 Motorola, Inc. Organic electroluminescence device with mixed hole transporting materials
KR20110029831A (ko) * 2009-09-16 2011-03-23 주식회사 진웅산업 유기 발광 화합물 및 이를 이용한 유기 전계발광 소자
KR20130121516A (ko) * 2012-04-27 2013-11-06 (주)위델소재 신규한 아릴아민을 사용한 정공 수송 물질 및 이를 포함한 유기 전계 발광 소자

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEN, C. H. ET AL.: "Highly stable organic light-emitting devices with a uniformly mixed hole transport layer", APPLIED PHYSICS LETTERS, vol. 87, no. 24, 2005, pages 243505, XP012076902 *

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JP2018048128A (ja) * 2016-09-14 2018-03-29 株式会社半導体エネルギー研究所 有機化合物、発光素子、発光装置、電子機器、及び照明装置
JP7140479B2 (ja) 2016-09-14 2022-09-21 株式会社半導体エネルギー研究所 有機化合物、発光素子、発光装置、電子機器、及び照明装置
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CN108383734A (zh) * 2017-02-03 2018-08-10 三星显示有限公司 胺类化合物和包括该胺类化合物的有机发光器件
US11744146B2 (en) 2017-02-03 2023-08-29 Samsung Display Co., Ltd. Amine-based compound and organic light-emitting device including the same
CN108383734B (zh) * 2017-02-03 2024-05-31 三星显示有限公司 胺类化合物和包括该胺类化合物的有机发光器件
US11121329B2 (en) 2017-11-24 2021-09-14 Samsung Display Co., Ltd. Amine compound and organic electroluminescence device including the same
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